The misery of Egyptian giants Zamalek continued after they waved goodbye to the African Champions League following a 2-2 draw at home to Libya's Ahli Tripoli in an exciting clash on Sunday.
The White Knights, who lost to South Africa's Mamelodi Sundowns in last year's final, needed to win their last Group B game to stand a chance of booking a last-eight berth but they let down their supporters in Alexandria with an error-ridden display.
They looked on course to grabbing the victory they craved when striker Bassem Morsi headed them in front after 13 minutes but paid the price of two dreadful mistakes as Ahli overturned the deficit.
Defender Mahmoud Hamdi was sent off just before the break when he earned a second yellow card for a needless foul on an opponent that gifted the Libyans a penalty, which Mohamed Ghanudi converted.
Another mistake, this time from goalkeeper Ahmed El-Shennawi, allowed Ahli to go 2-1 up in the second half when the Egyptian international's mis-calculated rush out of his goal allowed Vianney Mabide to beat him with an audacious long-range lob.
Nigerian midfielder Maarouf Yussuf brought Zamalek level with 15 minutes remaining but the White Knights failed to give their long-suffering fans something to cheer about, having also lost the Egyptian Premier League title to arch-rivals Ahly in a disappointing season.
Zamalek would have sneaked through on the head-to-head record if they had beaten Ahli Tripoli but they instead finished third in their group with five points from six matches.
USM Alger, who crushed Zimbabwe's Caps United 4-1 at home in the other group match, finished on top with 11 points and were joined in the quarters by second-placed Ahli, who bagged nine points.
Zamalek coach Augusto Inacio is likely to be sacked, with Maqassa's highly-rated manager Ihab Galal mooted as a possible successor.
Zamalek looked composed in the early exchanges, pressing hard in the final third as the scheme of deploying two strikers looked to have unsettled the Ahli defence.
They sent the 30,000 fans at Borg El-Arab Stadium into ecstasy after 13 minutes when Morsi met an inviting cross from left-back Mohamed Nassef with a bullet header that left the keeper with no chance.
Despite their territorial dominance, Zamalek's two central midfielders Maarouf Yussuf and Mahmoud Abdel-Aati struggled to contain Ahli's counter-attacks, with the visitors wasting a couple of chances to hit their opponents on the break.
Anis Saltou sent a glancing header just wide following a floated cross from the right and another side-footed effort from the towering striker narrowly missed the target.
Ahli's efforts were crowned on the stroke of halftime when they were awarded a penalty following a reckless sliding tackle from Hamdi, with Ghanudi sending the keeper the wrong way to silence the enthusiastic crowd.
Hamdi's dismissal left Zamalek with an uphill climb, with Ahli exposing their frailties to launch more dangerous counter attacks after the break.
One of those breakaways resulted in a second goal for Ahli which broke the hearts of the vociferous fans nine minutes past the hour mark.
Mabide picked up the ball in his own half and outpaced his marker to break clear from the halfway line. El-Shennawi's needless early rush out of his penalty area allowed the Central African player to lob the ball over him from 40 metres and into the back of the net.
Yussuf gave Zamalek a lifeline with a fine header that nestled into the net past the poorly-positioned keeper following a corner from substitute Mostafa Fathi but their late efforts to snatch a precious winner were in vain.
Ahli spurned several easy chances in the dying minutes but still got the job done on a tense night in Alexandria.